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<h1><a href="https://archiveofourown.org/works/23987920">The best kind of to do list</a> by <a class='authorlink' href='https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker'>troubleseeker</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>SPN kink bingo [6]</td></tr>

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>24/7, Anal Fingering, Anal Play, Anal Plug, Cock Cages, Dildos, Dom/sub, Established Relationship, M/M, Masturbation in Shower, Orgasm Denial, Sub Dean Smith, Webcam/Video Chat Sex, dom Sam Wesson</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-05-03</td></tr>

<tr><td><b>Updated:</b></td><td>2020-05-03</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-02 20:22:15</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,201</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/23987920</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean Smith has to go on a long, tedious business trip. It takes him away from his boyfriend slash dom Sam Wesson and is too boring to survive. Sam steps in with some tasks he needs Dean to do for his sir to make their time apart more bearable.<br/>Step one: take a shower<br/>Step two: unlock your dick ...<br/>step three: ...<br/>step four: profit?</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Dean Smith/Sam Wesson</td></tr>

<tr><td><b>Series:</b></td><td>SPN kink bingo [6]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1645564</td></tr>

<tr><td><b>Comments:</b></td><td>7</td></tr>

<tr><td><b>Kudos:</b></td><td>62</td></tr>

<tr><td><b>Collections:</b></td><td>SPN Kink Bingo 2020</td></tr>

</table>

<a name="section0001"><h2>The best kind of to do list</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Big ass thank you to <a href="https://archiveofourown.org/users/AnOddSock/pseuds/AnOddSock">AnnOddSock</a> for being my enthusiastic beta this!!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  <span>Dean checks his phone twice before getting in the cramped motel shower. Making sure it’s </span>
  <em>
    <span>actually</span>
  </em>
  <span> recording, and not balanced too precariously against the little travel shampoo bottles.</span>
</p><p>
  <span>“Hey, Sammy. I mean, sir.” Dean gives the camera a little wave and turns the water on. Making sure he’s facing the camera he reaches for the soap and gets to work. Nice ‘n clean. Just washing himself. Not thinking about anything sexy.</span>
</p><p>
  <span>When he’s all washed, he turns down the shower a bit; letting his voice sound above the rush of water.</span>
</p><p>
  <span>“Ok.” He announces to the room. Breathing a bit harder now. “I’ve uh- got the key here.” He lifts the small thing, threaded on a thin chain around his neck. “Haven’t used it till now, promise.”</span>
</p><p>
  <span>His hands are slippery when he tries to unlock the cage locked nice and snug around his cock, but he makes it work. The pieces slide apart neatly, and he gives them a rinse before setting them aside and focusing on his soon to be audience once more.</span>
</p><p>
  <span>“Thank you for letting me out, sir.” He tells the empty bathroom, cheeks heating more than the water can be blamed for. He backs up, shoulders against the tiles and legs stepping wider. He’s putting himself on display. “So happy I can be hard for you.”</span>
</p><p>
  <span>One arm up, the instructions had said, so Dean reaches up and curls one hand behind his head; out of the way. Sam always likes making him stretch out; makes him look lean or something.</span>
</p><p>
  <span>His other hand finds its natural way to his hard as nails dick, but he doesn’t stroke, not yet. This is going to be over so fast already. If he wants to savor being out, being hard- he’ll need to start gently. It’s all for Sam, of course. This isn't </span>
  <em>
    <span>exactly </span>
  </em>
  <span>about him.</span>
</p><p>
  <span>He breathes in the steam, eyes the camera through hooded eyes. It’s a stay of execution he can’t draw out forever. And not because Sam would be angry at him for going slow- nah, it’s cause Dean is too impatient.</span>
</p><p>
  <span>“One.” He sighs after a deep breath, no longer able to wait, and moves his hand in a slow stroke. Balls to tip, and back down.</span>
</p><p>
  <span>“Two.” Dean’s head falls back, biting at his lip already. It’s too much; too soon and too late.</span>
</p><p>
  <span>“Three. Oh-” Dean knows he’s not allowed to come, knows he’s only got so many strokes before he has to lock himself back up, but he still speeds up. “Four. Fuck- five.”</span>
</p><p>
  <span>Sam is a good dom, and he’s got a thing for cages. They’ve been playing with them for years now, and Dean knows the ins and outs of most of the cages on the market. Sam loves putting Dean in one and keeping the key hidden away till they’re both desperate and high on lust. But having Dean carry that key and every last drop of responsibility by </span>
  <em>
    <span>himself</span>
  </em>
  <span>? That’s better.</span>
</p><p>
  <span>Or worse.</span>
</p><p>
  <span>“Nine.” Dean bites out, body tense already and he’s barely had any friction. His balls are tight and full; so ready to get this over with. “Shit, sir. Feels so good. Thank you. Oh, fuck- ten.”</span>
</p><p>
  <span>When he counts out a stuttering fourteen, Dean knows he’s only got one more left. His arm trembles with exertion. He doesn’t want to lose that last tiny bit of friction, but if he moves now he’s finished till Sam sends more instructions.</span>
</p><p>
  <span>Of course, he could stand here and record himself being a brat and wank till he spills too. He could even lie and say his camera wasn’t working or he accidentally deleted the vid. There’s another week till he’s back home; Sam wouldn’t know… maybe.</span>
</p><p>
  <span>“Fifteen.” It takes force to make himself let go. Dick bobbing red and miserable between his legs as he breathes. “Thank you, sir.” </span>
</p><p>
  <span>Dean stands still, taking measured breaths under the warm water till he can feel his dick grumpily shrink back into hibernation mode. No cold shower today; score.</span>
</p><p>
  <span>He’s silent when he locks his dick back up. Crimes unknown.</span>
</p><p>
  <span>Dean angles his hips so Sam gets a good view of his work. Clean and denied, dicklet locked away till Sam lets him out again.</span>
</p><p>
  <span>The curl of heat that’s trapped in between his legs isn’t uncomfortable. They wouldn't do this if either of them didn’t like it. The pressure in his nuts is a reminder of how </span>
  <em>
    <span>good</span>
  </em>
  <span> he’s being. It’s a warm hug from Sam even when he’s miles and miles away. It’s soothing- kinda. Sam will be proud, and he’ll tell Dean exactly that once he’s sent the vid. </span>
</p><p>
  <span>“Thank you for letting me jerk myself for you, sir. It felt really good.”</span>
</p><p>
  <span>Two more instructions to follow first, though. Sam is nothing if not thorough.</span>
</p><p>
  <span>Making sure he’s not about to fall flat on his face, Dean turns around and gives the camera a nice shot of his ass.</span>
</p><p>
  <span>“Kept it in all day.” He says, reaching back to pull his cheeks apart; shows off the thick plug buried there. “Made me think of you, sir.”</span>
</p><p>
  <span>It isn’t the biggest toy they owned, wasn’t even the biggest one Sam had put in his travel toy box, but it’s one of Dean’s favorites. Something about its shape had it pressing against his prostate every so often. </span>
</p><p>
  <span>The ones that kept up constant stimulation were fun too of course, but they made concentrating very hard which meant they were impossible to use while he worked. No one cared if he twitched or coughed every so often, but his boss would not hesitate to fire him if he was drooling onto his notes during a meeting.</span>
</p><p>
  <span>No one else has to know what he and Sam got up to in private.</span>
</p><p>
  <span>One-handed, he rotates the plug. Out a bit, twist to the side, push back in. Out, twist, in. Out, twist. In. Till he can’t hold back his little sighs of delight.</span>
</p><p>
  <span>“Fuck- wish this was you, sir. Miss you so much.” </span>
</p><p>
  <span>Panting against slick tile, Dean picks up his pace, stretching his rim wide and then punching the plug back in. He’s not aiming for his prostate, but he ends up hitting it every so often anyway. </span>
</p><p>
  <span>If his dick wasn’t locked away, it would be singing right now. Instead, it just drools against the tiles every so often. </span>
</p><p>
  <span>When he’s sure he can’t take any more, Dean finally pulls the plug out all the way. He drops it at his feet, ready for a wash later, and uses both of his hands to stretch his ass wide open; showing off just how good he’s been.</span>
</p><p>
  <span>He catches his breath, clenching and releasing for Sam’s viewing pleasure, before fumbling for the shower controls and shutting off the water all the way. He walks closer to the camera when he’s out; dripping wet and flushed red from water that was a tad too warm but the perfect distraction from- well, his dick. </span>
</p><p>
  <span>“Love stretching myself open for you, sir. Can’t wait to take your dick.”</span>
</p><p>
  <span>He pauses the recording to dry off, and move to the bedroom portion of his hotel space. He’d already laid out his next partner and the extra towels he’d asked for in his reservation. The phone gets a spot on the nightstand with a great view of his little scene. </span>
</p><p>
  <span>“Got everything you told me to use, sir.”</span>
</p><p>
  <span>He gestures at the toy, one of Dean’s favorites. They’d had a ton of fun making it; a perfect copy of Sam’s dick. Not as good as the real thing, but it was a taste from home.</span>
</p><p>
  <span>He makes sure to throw bedroom eyes at the blinking red light and gives the dildo a bit of oral love. Kisses, licks, and then the clutch of his throat. He’s breathing hard when he thanks Sam for letting him suck his dick.</span>
</p><p>
  <span>Lube is next, stroked hastily but lovingly onto the toy. He’s open and wet already, but there’s truly no such thing as too much lube.</span>
</p><p>
  <span>“So glad you packed this one.” He tells camera Sam, getting on his hands and knees; ass angled towards the viewfinder. The base of the dildo rests on the towel, Dean’s hand holding it rock steady as he sinks his well-stretched hole down onto the tip. </span>
</p><p>
  <span>The instructions Sam had sent him earlier in the day clearly stated ‘fuck yourself on my dick slowly’ so Dean has to hold back and not slam himself down onto the toy. God, he wants it in. He’s been thinking about it all day. Dick trying desperately to get hard every single time he imagined it. The sweet, thick slide of Sam inside of him.</span>
</p><p>
  <span>“God, feels so good.” He gasps, face smushed into the sheets. “Want it all, sir. Want it so bad. Please, please let me have it.”</span>
</p><p>
  <span>Sam’s not there to tell him it’s ok to ignore the written commands, but he can’t help but beg. He keeps up the unbearably slow slide down, down, down- till his ass is on the towel and he’s perfectly full of ‘Sam’. </span>
</p><p>
  <span>“Oh yeah.” He sighs. “That’s the stuff.”</span>
</p><p>
  <span>The gentle sex is soothing. Pretty much exactly what Dean needs after a hectic day of meetings and numbers and </span>
  <em>
    <span>no Sam</span>
  </em>
  <span>; that last one is the worst of the bunch. They’re usually joined at the hip once they’re both home.</span>
</p><p>
  <span>It’s not too strenuous or aggressive enough to let him feel it tomorrow, but just enough to settle his nerves and needy hole. </span>
</p><p>
  <span>He fucks himself till his thighs burn, switching position twice to show the camera different important details. The trained stretch of his ass as he pushes down. The wink of his hole when he pulls off, waits, and then plunges back down. The bounce of his caged cock as he sinks down as if he was straddling Sam. Even closer, the sluggish drip of precome worming its way out of him as he nails his prostate.</span>
</p><p>
  <span>There’s no time limit here, no real end goal except sending Sam something hot. So Dean fucks himself till he’s had his fill, flushed enough that he might need another shower.</span>
</p><p>
  <span>“Thank you for letting me play, sir. Love you.” </span>
</p><p>
  <span>He’s been moaning and whimpering endearments and curses the whole time, lost in the feeling of working himself nice and deep.</span>
</p><p>
  <span>“Miss you, sir. Sam.” </span>
</p><p>
  <span>Smiling warmly, he pulls the dildo out and presses a kiss to the slick tip before reaching over to turn off the camera. Leaving the toys and cleanup for later, he checks the recording and sends it to his boyfriend. It’ll take a while, there’s 25 minutes of footage, so Dean stretches till his neck cracks and cleans up the remnants of the scene.</span>
</p><p>
  <span>Only a week left, and then they’ll be able to touch for real again. </span>
</p><p>
  <span>Until then he waits for his message to be marked ‘seen’.</span>
</p><p>
  <em>
    <span>‘Such a good boy</span>
  </em>
  <span>’ Sam replies when Dean’s done with his second shower. </span>
  <em>
    <span>‘You plug up after?’</span>
  </em>
</p><p>
  <span>Sam probably thinks he’s sleeping already, and yeah- he probably should head for bed. It’s late. </span>
</p><p>
  <em>
    <span>No</span>
  </em>
  <span> he taps back, choosing to not call.</span>
</p><p>
  <em>
    <span>‘Good’</span>
  </em>
  <span> Comes back almost instantly. </span>
  <em>
    <span>‘My obedient pet. I’m so lucky to have you’</span>
  </em>
</p><p>
  <span>Three dots continue to flicker at the bottom of the screen. Dean gets comfortable in his hotel bed, downing the last of his post-game rehydration water.</span>
</p><p>
  <em>
    <span>‘I’ll send you some more instructions tomorrow after lunch, how was your day?’ </span>
  </em>
  <span>The switch from dom to lover is soft but clear for Dean. He slaps at the switch by the bed til the room turns dark.</span>
</p><p>
  <em>
    <span>Not that bad, but omg Uriel is a dick. </span>
  </em>
</p><p>
  <em>
    <span>‘You in bed?’</span>
  </em>
</p><p>
  <em>
    <span>Mhm, boss wants us to have a breakfast meeting at 7.30 but the coffee here sucks ass so I’m checking out a local shop first</span>
  </em>
</p><p>
  <em>
    <span>‘Not paid enough to deal with assholes without caffeine?’ </span>
  </em>
  <span>Sam guesses, and Dean snorts.</span>
</p><p>
  <em>
    <span>Something like that, yeah. </span>
  </em>
  <span>After a moment’s hesitation, he adds: </span>
  <em>
    <span>miss you</span>
  </em>
</p><p>
  <span>It’s easier to admit feelings like that while he’s in subspace. Even a quick shallow dip of the toes like this is technically an excuse to get sappy. But it’s true. He misses Sam’s goodnight kisses and anaconda hugs.</span>
</p><p>
  <em>
    <span>‘Miss you too Dean, just a couple of days and I’ll show you just how much’</span>
  </em>
</p><p>
  <span>For half a second, Dean imagines letting his inner brat out to play and question Sam’s chastity. There was no promise made, but Dean’s going to be disappointed if he’s not dripping in come by the end of their welcome home session.</span>
</p><p>
  <em>
    <span>Can’t wait! </span>
  </em>
  <span>He types instead, and it’s technically true. He’s still working on asking things for himself.</span>
</p><p>
  <em>
    <span>‘Good night, Dean. Sleep tight.’</span>
  </em>
</p><p>
  <span>Dean’s halfway through tapping his own kisses and hugs when </span>
  <em>
    <span>‘Did you have a snack and drink?’</span>
  </em>
  <span> pops up on his screen. Typical Sam, remembering he needs to take care of his disaster boyfriend as well as torture him.</span>
</p><p>
  <em>
    <span>I promise to sleep like a rose, the bed’s pretty good, even if it doesn’t have you in it. And yes, I had a glass of water and some chocolate.</span>
  </em>
</p><p>
  <em>
    <span>‘Good boy. Love you, man. Talk to you tomorrow.’</span>
  </em>
</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>If you want to come yell at me on <a href="http://ryugarika.tumblr.com/">tumblr</a> ... feel free to, I can take it.</p><p>Comments feed me!</p></blockquote></div></div>
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